How Far Should CEOs Go

This week I received one of the most extraordinary emails from a fellow Founder and CEO. The subject line was: “Protect democracy, vote for Biden.” I knew it wasn’t sent to only me because I could see a shared inbox at WeSpire had received it as well.  I also don’t know CEO David Barrett, but I know his company Expensify well. They are a high-flying, billion-dollar plus company that makes expense management simple and easy. We use them at WeSpire.

In fact, Expensify has 10M users. And every single one got this email.

At first, I thought it was a mistake. Certainly I have received emails from friends asking me to support various candidates. But I can’t think of a time when I have received, as a customer, an email from a company asking me to vote for one candidate over another. Did he really mean to send this to every single Expensify customer? Yes, he did.

Since receiving the message, I have read quite a bit about what has become a controversial email. But what has struck me is that sending this email was David Barrett’s idea, but not his decision. The culture at Expensify is itself highly democratic. Employees were not only asked to edit drafts of the email but, ultimately they voted to send it or not. It required and received a supermajority to send.

Barrett also acknowledges in the letter that sending it is unusual. “I wouldn’t be sending this email if this election were just about ‘normal issues’ — taxes, legislative priorities, healthcare, etc.,” Barrett wrote. “But it isn’t. This election is a referendum on what limits, if any, we place on our elected leaders to govern us in a fair and representative way. This election will decide if widespread voter suppression is an acceptable governing tactic.”

Barrett and his team’s decision stands in stark contrast to other companies who have deliberately told employees to avoid political conversations. Coinbase recently banned employee activism at work. They declared an “apolitical culture,” which prompted 60 plus employees to leave. Barrett criticized Coinbase’s approach for what he said was pretending to be apolitical while actually supporting the status quo.

“If you are a member of a democratic society, you can’t opt out of that. Choosing not to participate is also a choice — that is a political decision,” he said. “If you are a company that chooses not to engage, that either means: one, our official company stance is that we like the status quo and want to keep it; or two is, we don’t like the status quo, but we’re too cowardly to do anything about it.”

I don’t agree at all with the Coinbase decision. Yet, I also can’t imagine sending every one of our registered users an email like Expensify, even though I agree personally with the premise. The entire debate has made me pause and ask myself: am I being a coward?

Where I have landed is that, as a company, we should be politically active around issues critical to a just, equitable, healthy, and democratic society. So far that includes giving the WeSpire team Election Day off, so they can have time to vote for whatever candidate they choose. Likewise, Wespire is vocal about being part of the Tech Compact for Social Justice, Time to Vote, and supporting the Paris Accord. I truly wish these were goals that, at a high-level, both parties agreed on. We could spend our time debating the best policies to achieve equality and justice, representative democracy, and climate stabilization—not whether they are necessary. But that is not our world in 2020.

I have chosen, as a CEO, to make my opinions on certain topics clear to my employees and by writing Saturday Spark to many others as well. But I have drawn a line at sharing my opinions directly with our users. They didn’t choose WeSpire. Their company did. If our users hear a strong opinion from someone about the critical issues facing our nation, it should be from their leadership, not us.

I think what the team at Expensify did was incredibly bold and consistent with their values. I am proud to be their customer. I hope it encourages every recipient to vote, and to cherish the right to vote, no matter who they ultimately support. I also hope we don’t come to regret where we drew the line.

Quote of the Week: “We must always take sides. Neutrality helps the oppressor, never the victim. Silence encourages the tormentor, never the tormented. Sometimes we must interfere.”

Elie Wiesel

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